Utilization of tetraethylammonium cyanide for preparation of cyclopentadienyl iron cyanocyclohexadienyl complexes. Study of their electrochemical and chemical oxidation. was written by Guennec, N.;Moinet, C.. And the article was included in Journal of Organometallic Chemistry in 1995.Product Details of 64113-86-6 This article mentions the following:
Addition of Et4NCN to a solution of (η5-cyclopentadienyl)(η6-arene)iron(1+), in MeCN was studied by voltammetry. With electron-withdrawing groups such as nitro, keto, sulfone, azo and azoxy bonded to the arene, the reaction occurs immediately and a wave resulting from oxidation of hexadienyl species is observed in the range 0-1V vs. SCE. Preparation of various hexadienyl compounds, e.g. I (X = NO2, COPh, SO2Ph) was achieved with good yields. To obtain ortho-substituted benzonitriles, electrochem. and chem. oxidations of hexadienyl complexes were compared. The best results were obtained with N-bromosuccinimide (NBS) and a demetalation generally occurs. A 1-pot synthesis of benzonitrile compounds can be achieved after addition of cyanide ion and then NBS to a solution of (η5-cyclopentadienyl)(η6-arene)iron(1+) in MeCN. [CpFe{η6-C6H5N(O):NC6H4CN-2}]+ is directly obtained from the azoxy dicationic compound [(CpFe)2(PhN(O)NPh)]2+. In the experiment, the researchers used many compounds, for example, 5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6Product Details of 64113-86-6).
5-Methyl-2-nitrobenzonitrile (cas: 64113-86-6) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Product Details of 64113-86-6
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts